[ CAS No. 36234-66-9 ]

Name: 2-Amino-6,7-dihydrobenzo[d]thiazol-4(5H)-one
Brand: Ambeed
SKU: A205611
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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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SDS

Product Details of [ 36234-66-9 ]

CAS No. :	36234-66-9	MDL No. :	MFCD21117211
Formula :	C₇H₈N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AYSCUQOLIIAARX-UHFFFAOYSA-N
M.W :	168.22	Pubchem ID :	21941906
Synonyms :

Computed Properties of [ 36234-66-9 ]

TPSA :Topological Polar Surface Area	84.2	H-Bond Acceptor Count :	4
XLogP3 :	1.1	H-Bond Donor Count :	1
SP3 :	0.43	Rotatable Bond Count :	0

Safety of [ 36234-66-9 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 36234-66-9 ]

Upstream synthesis route of [ 36234-66-9 ]
Downstream synthetic route of [ 36234-66-9 ]

[ 36234-66-9 ] Synthesis Path-Upstream 1~8

1
[ 24829-91-2 ]
[ 17356-08-0 ]
[ 36234-66-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	for 15.00 h; Reflux	General procedure: A mixture of 3-bromocyclohexane-1,2-dione 3 (50 mg, 0.26 mmol) and pyridine-4-carbothioamide (24.1 mg, 0.17 mmol) in EtOH (0.69 mL) was heated to reflux and stirred for 15 h. The reaction mixture was diluted with DMSO (0.5 mL) to completely dissolve all solids and the resulting mixture was purified by directly injecting the reaction mixture into a preparatory HPLC (C₁₈, water/acetonitrile/ammonium acetate buffer) to give 2-(pyridin-4-yl)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (30.4 mg, 0.13 mmol, 76percent) (Table 1, entry 1).
47%	at 90℃; for 16.00 h;	Int-35 (5.0 g, 26.17 mmol) was dissolved in EtOH (50 mL) and thiourea (1.99 g, 26.17 mmol) was added at rt. Then the mixture was heated at 90 °C for 16 h. After cooling down to rt, the mixture was concentrated under reduced pressure and the residue was diluted with water (50 mL) and extracted with EtOAc (2 x 150 mL). Combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by colunm chromatography on reversed phase silica gel using water/acetonitrile with 0.01percent formic acid as eluent. 2-Amino-6,7-dihydrobenzo[d]thiazol-4(5H)-one (int-36) was obtained as an off-white solid in 47percent (2.1 g) yield. MS (ESI) mlz 169.01 [M-H].

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 28, p. 3633 - 3635
[2] Patent: WO2018/81612, 2018, A1. Location in patent: Paragraph 0302
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 19, p. 5879 - 5882

2
[ 765-87-7 ]
[ 36234-66-9 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 28, p. 3633 - 3635
[2] Patent: WO2018/81612, 2018, A1

3
[ 36234-65-8 ]
[ 36234-66-9 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1971, vol. 313, p. 1125 - 1130

4
[ 5220-49-5 ]
[ 36234-66-9 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1971, vol. 313, p. 1125 - 1130

5
[ 24829-91-2 ]
[ 17356-08-0 ]
[ 36234-66-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	for 15.00 h; Reflux	General procedure: A mixture of 3-bromocyclohexane-1,2-dione 3 (50 mg, 0.26 mmol) and pyridine-4-carbothioamide (24.1 mg, 0.17 mmol) in EtOH (0.69 mL) was heated to reflux and stirred for 15 h. The reaction mixture was diluted with DMSO (0.5 mL) to completely dissolve all solids and the resulting mixture was purified by directly injecting the reaction mixture into a preparatory HPLC (C₁₈, water/acetonitrile/ammonium acetate buffer) to give 2-(pyridin-4-yl)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (30.4 mg, 0.13 mmol, 76percent) (Table 1, entry 1).
47%	at 90℃; for 16.00 h;	Int-35 (5.0 g, 26.17 mmol) was dissolved in EtOH (50 mL) and thiourea (1.99 g, 26.17 mmol) was added at rt. Then the mixture was heated at 90 °C for 16 h. After cooling down to rt, the mixture was concentrated under reduced pressure and the residue was diluted with water (50 mL) and extracted with EtOAc (2 x 150 mL). Combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by colunm chromatography on reversed phase silica gel using water/acetonitrile with 0.01percent formic acid as eluent. 2-Amino-6,7-dihydrobenzo[d]thiazol-4(5H)-one (int-36) was obtained as an off-white solid in 47percent (2.1 g) yield. MS (ESI) mlz 169.01 [M-H].

6
[ 765-87-7 ]
[ 36234-66-9 ]

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 28, p. 3633 - 3635
[2] Patent: WO2018/81612, 2018, A1

7
[ 36234-65-8 ]
[ 36234-66-9 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1971, vol. 313, p. 1125 - 1130

8
[ 5220-49-5 ]
[ 36234-66-9 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1971, vol. 313, p. 1125 - 1130

[ 36234-66-9 ] Synthesis Path-Downstream 1~6

1
[ 36234-66-9 ]
[ 70590-48-6 ]

Yield	Reaction Conditions	Operation in experiment
52%	With isopentyl nitrite; In tetrahydrofuran; at 0 - 45℃; for 3.0h;	Int-36 (1.0 g, 5.95 mmol) was dissolved in tetrahydrofuran (20 mL) and isoamyl nitrite (0.95 mL, 7.14 mmol) was added at 0 °C. Then the mixture was heated at 45 °C for 3 h. After cooling to rt, the mixture was quenched with aq. ammonium chloride and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with water (30 mL), brine (30 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by colunm chromatography on neutral alumina using 5percent EtOAc in hexane as eluent. 6,7- Dihydrobenzo[d]thiazol-4(5H)-one (int-37) was obtained as an off-white solid in 52percent (480 mg) yield. ?H-NMR (400 MHz, DMSO-d6): oe 8.95 (s, 1H), 3.13 (t, J= 6.0 Hz, 2H), 2.60-2.53 (m, 2H), 2.13 (dt, J= 12.4, 6.4 Hz, 2H); MS (ESI) mlz 154.13 [M+Hj.

Reference： [1]Patent: WO2018/81612,2018,A1.Location in patent: Paragraph 0303

2
[ 765-87-7 ]
[ 36234-66-9 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 3633 - 3635
[2]Patent: WO2018/81612,2018,A1

3
[ 24829-91-2 ]
[ 17356-08-0 ]
[ 36234-66-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	In ethanol; for 15.0h;Reflux;	General procedure: A mixture of 3-bromocyclohexane-1,2-dione 3 (50 mg, 0.26 mmol) and pyridine-4-carbothioamide (24.1 mg, 0.17 mmol) in EtOH (0.69 mL) was heated to reflux and stirred for 15 h. The reaction mixture was diluted with DMSO (0.5 mL) to completely dissolve all solids and the resulting mixture was purified by directly injecting the reaction mixture into a preparatory HPLC (C18, water/acetonitrile/ammonium acetate buffer) to give 2-(pyridin-4-yl)-6,7-dihydrobenzo[d]thiazol-4(5H)-one (30.4 mg, 0.13 mmol, 76percent) (Table 1, entry 1).
47%	In ethanol; at 90℃; for 16.0h;	Int-35 (5.0 g, 26.17 mmol) was dissolved in EtOH (50 mL) and thiourea (1.99 g, 26.17 mmol) was added at rt. Then the mixture was heated at 90 °C for 16 h. After cooling down to rt, the mixture was concentrated under reduced pressure and the residue was diluted with water (50 mL) and extracted with EtOAc (2 x 150 mL). Combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by colunm chromatography on reversed phase silica gel using water/acetonitrile with 0.01percent formic acid as eluent. 2-Amino-6,7-dihydrobenzo[d]thiazol-4(5H)-one (int-36) was obtained as an off-white solid in 47percent (2.1 g) yield. MS (ESI) mlz 169.01 [M-H].

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 3633 - 3635
[2]Patent: WO2018/81612,2018,A1.Location in patent: Paragraph 0302
[3]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5879 - 5882

4
[ 540-80-7 ]
[ 36234-66-9 ]
[ 1280703-98-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5879 - 5882

5
[ 5220-49-5 ]
[ 36234-66-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1971,vol. 313,p. 1125 - 1130

6
[ 36234-65-8 ]
[ 36234-66-9 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1971,vol. 313,p. 1125 - 1130

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Code	Phrase
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P330	Rinse mouth.
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P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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P370 + P378	In case of fire:
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
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H301	Toxic if swallowed
H302	Harmful if swallowed
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H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
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H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 36234-66-9 ]

Quality Control of [ 36234-66-9 ]

Related Doc. of [ 36234-66-9 ]

Product Details of [ 36234-66-9 ]

Computed Properties of [ 36234-66-9 ]

Safety of [ 36234-66-9 ]

Application In Synthesis of [ 36234-66-9 ]

[ 36234-66-9 ] Synthesis Path-Upstream 1~8

[ 36234-66-9 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 36234-66-9 ]

Amines

Ketones

Related Parent Nucleus of [ 36234-66-9 ]

Aromatic Heterocycles

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 36234-66-9 ]

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[ 36234-66-9 ]